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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Annapolis Guesthouse - Completely Separate Space
2 bedrooms, 3 beds, 1 private bathroom
29 Aug – 3 Sept
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4.87 out of 5 average rating, 215 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds, 4 bathrooms
24–29 Aug
New place to stay
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA and Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Aug
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 466 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 185 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
6–11 Aug
4.93 out of 5 average rating, 59 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 360 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
4.97 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 58 reviews
Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.94 out of 5 average rating, 446 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 366 reviews